Luke wears 14kt gold chain necklace JENNIFER FISHER, woven fedora BAILEY HATS
Luke wears cotton denim blend shirt BILLY REID, 14kt gold chain necklace JENNIFER FISHER

When you’re in the business of profiling people, you don’t often get to revisit the same subject, and when you do, it isn’t always pleasant. Maybe they didn’t like how you described their career, or the way you printed what they said, verbatim. Celebrities can be funny that way. Luke Flynn proved a wonderful exception, and speaking to him again after eleven years had me smiling from ear to ear. The kid turned out alright.

We hadn’t seen each other since 2003, when the New York Times sent me to Port Antonio, Jamaica to interview the then-27-year-old grandson of the swashbuckling actor Errol Flynn, who was modeling for Tommy Hilfiger. The younger Flynn was living with his grandmother, Patrice Wymore Flynn, on Errol’s 1,700-acre cattle farm, which had recently been ravaged by a hurricane. Needless to say, spliffs and Red Stripes were passed. He described his routine at the time thus: “Wake up, surf, eat lunch, surf, swim, hang out, maybe go into town at night.” There was a little beach spot he’d hit up with his pals or a gal, “just to lay back and look up at the stars and play drums.”

Luke wears cotton floral shirt DRIES VAN NOTEN, striped cotton drawstring pants BILLY REID
Sky wears swimsuit HERMÈS, striped draw string pants BILLY REID
Luke wears swim shorts LOUIS VUITTON

But like that other talented beach-bongo aficionado, Matthew McConnaughey, Luke Flynn, dreamer-dilettante, has since sprouted the wings his grandmother told me he needed time to grow. And then some.

These days, he’s still surfing his tail off, but he’s also just optioned three movie scripts, one of which he’s directing himself. He’s making a trancehall record with his lovely Jamaica-born girlfriend, the actress and recording artist Sky Nicole Grey, and still has his Miami-based clothing business, which he owns with his step-mom, Posh Vintage. A fair-haired, lanky limbed devil like his grandad, he pulls in extra scratch from modeling, too.

Luke wears printed short sleeve shirt BILLY REID, gold frame aviators RAY-BAN
Sky wears bikini ERES

Don’t hold him to it, but he says he’s done with acting for now. He’s got the writing bug and sees his future behind the camera. Realizing how adult and disciplined this all sounds for a kid that grew up like Tom Sawyer marooned on Treasure Island, he says with a laugh: “I’m trying to get back to that place. But I guess I found a real life.”

Flynn recently moved back to the compound in Port Antonio fulltime to save the family farm from potential develpment, fix up the main house, and care for his 87-year-old grandma. He says the ranch is out of hock and thriving now, with 400 head of cattle. “The next crop is coconuts,” he says. “We’re going in heavy.”

Sky wears snakeskin bikini STELLA MCCARTNEY, headscarf LEM LEM, classic wayfarers RAY-BAN
Luke wears printed short sleeve shirt BILLY REID, gold frame aviators RAY-BAN
Sky wears bikini ERES

He’s also restoring several buildings on the property, including the modernist homestead his grandfather built himself in the mid-1950s. Luke’s childhood buddies who, I met last time around – Jermane, Omar, and Errol – are still by his side, and are even acting in his films.

But mostly he’s there for grandma Patrice, whose marriage to Errol lasted eight years. “She’s not doing so hot,” Luke says. “I need to be there if she falls and can’t get up. She has a lady living with her, but she wants to be 100-percent independent. She can’t drive anymore but she wants to. She’s still drinking rum and smoking cigarettes, a butt in one hand and an oxygen tank in the other.” He laughs. “It’s like she’s the 21-year-old now, not me.”

Luke wears knit cardigan MICHAEL BASTIAN, striped cotton drawstring pants BILLY REID, 14kt gold chain necklace JENNIFER FISHER
Sky wears bikini ERES earrings ILEANA MAKRI
Luke wears cotton henley AG ADRIANO GOLDSCHMIED, swim shorts JACK SPADE, gold frame aviators RAY-BAN
Sky wears snakeskin bikini STELLA MCCARTNEY, classic wayfarers RAY-BAN

In recent years, he’s taken a great deal of inspiration from his grandfather’s books. (Were there ever a doubt about his brilliance, pick up Errol’s 1959 memoir, My Wicked, Wicked Ways, which reads like it was written yesterday.)

One of the scripts he’s had optioned, In Like Flynn, is based on Errol’s 1937 adventure novel, Beam Ends, about a disastrous boat journey he took with a group of friends before he landed in Hollywood. The film he’s directing, Jamrock, is more his own story, about a crew of treasure-hunting surfers. (He kept the casting local, and is super stoked about landing Crazy Jim, “the Robert DeNiro of Jamaica.”)

Luke wears cotton blend sweater JACK SPADE
Sky wears tie-dye top and bottom RAQUEL ALLEGRA body chain JENNIFER FISHER

He credits the island with making him who he is today. “The fact that it’s a Third World country really gives you great perspective,” he says. “It makes it easy to appreciate the small stuff in life, and understand that the best things really are free.”

He says he does regret one thing, though. “I wish I could have met my Grandpa,” he says. “He really made his life into his own adventure and seized it with both hands.” Hold on tight, my friend.

Luke wears floral cotton polyamide blend jacket DRIES VAN NOTEN
cotton blend cargo pant RALPH LAUREN
14kt gold chain necklace JENNIFER FISHER
woven fedora BAILEY HATS
grooming by MIRA CHAI
special thanks to the TRIDENT HOTEL, JAMAICA